In this chapter, I will reflect on my experience in Monrovia 2010–2013 as an expatriate concert promoter participating in the local music industries, 1 and the subsequent research in 2014 as a consultant to the World Bank at a time when the sector was considered for inclusion in the country’s Private Sector Development Strategy (PSDS). Using the autoethnographic method (Chang 2008; Ellis et al. 2010), I will interrogate my participant observation as a cultural outsider, privileged foreign expert and local stakeholder, and revisit the research output I produced for the World Bank. Literature from cultural policy, media, and development studies will frame the analysis of the roles of culture 2 in aid and development which I witnessed on the ground in Liberia, noting both flaws and positives. Acknowledging the discourse and institutional frameworks constraining the current path towards supporting musicians as that of the creative and cultural industries (CCIs), I reflect on why more integration of informal activity would be useful in future efforts at strategic music industry sector expansion in Liberia, rather than a punitive approach towards the informal sector.